Download e-book for kindle: Acyclic, Carbocyclic and L-Nucleosides by L. Agrofoglio, S.R. Challand

By L. Agrofoglio, S.R. Challand

ISBN-10: 9400708165

ISBN-13: 9789400708167

ISBN-10: 9401037345

ISBN-13: 9789401037341

Interest in chemical entities able to blocking off or editing phone metabolism eventually is going again to the invention of the constitution of DNA within the Nineteen Fifties. figuring out of the biochemical techniques taken with cellphone metabolism swiftly resulted in the concept that compounds will be designed which would intervene with those procedures, and hence may be utilized in the therapy of the illnesses attributable to viral an infection. considering that then, a number of periods of gear were came across which count for his or her influence on amendment of the right kind functioning of nucleic acids and, with the creation of acyclovir for the therapy of Herpes infections, nucleoside analogues became the cornerstone of antiviral chemotherapy.
The luck of the early nucleoside brokers, the toxicity and metabolic instability of many nucleoside analogues, and the consequences of viral pathogens on public overall healthiness are riding the layout, synthesis and review of recent nucleoside analogues, with a lot consciousness turning to nucleosides containing `non ordinary' sugar analogues. This e-book specializes in the advance of those brokers, and attracts jointly the entire to be had fabric in an simply consulted shape, which while courses the reader into the examine literature at the topic. Written basically for the medicinal chemist, assurance contains either man made techniques and description assistance at the major traits in organic job. specific recognition is attracted to the comparability of artificial routes to compounds with their average analogues. ultimately, the real antiviral actions of the compounds are taken care of, together with anti-retrovirus, anti-hepadnavirus and anti-herpes virus homes.
Written often for medicinal chemists within the pharmaceutical and artificial natural chemists in academe, this ebook may also be appealing to researchers in associations concentrating on mobile metabolism. complicated scholars of natural chemistry will locate the transparent dialogue of the substitute options followed within the improvement of those compounds an invaluable creation to this interesting and tough area.

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Extra info for Acyclic, Carbocyclic and L-Nucleosides

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Some purine carba-acyclic nucleosides were prepared by Yuan et al. 19. 14 [a] H,N ~1i N 128 NH, + Br, /0, 'V" o /"-.. 18 133aR=OH b R = NH, 45 46 ACYCLIC, CARBOCYCLIC AND L-NUCLEOSIDES NL HN~JlCI • + NL n-BuOH RNH. , H+ HN~JlNHR • O-SOC 135 CI Zn,H+ ~ I HN~N • NL~ (EtO),CH, N : x NH. AcNMe. l. 5 Prodrugs and other derivatives of acyclovir Acyclovir is a highly selective inhibitor of HSV -1 and 2 replication. In virally infected cells it is phosphorylated by the virally encoded thymidine kinase to the monophosphate [95], then further metabolized to the triphosphate which is the active form of the drug [96,97].

47] reported the resynthesis of some of these compounds as 5'-deoxy-5'-p-(ftuorosulfonyl)benzoyl esters with the object of evaluating their potential as inhibitors of human purine nucleoside phosphorylase (PNP) [48-50). The 5'-deoxy-5'-iodo derivatives were also synthesized using Moffat's procedure [51], but neither series proved to be of further interest. Beauchamp et al. 6), but again none of these compounds were of lasting biological interest. The synthesis of the 7-deazaguanine analogue 50 was also previously reported by Seela et al.

Uracil and cytosine analogues have been also prepared by Schroeder et al. 12 ether. 2 JlM). It was made [82] by alkylation of the silylated 5-fluoro-6-thiomethyl uracil. The initially obtained acyclic nucleoside was then transformed into the 5-fluorocytosine analogue and subsequently by deamination into the desired uracil. -:; THF N B'~CH,OH NaBH, - - -... 15 R,R,NH CH,OH R·CI 42 ACYCLIC, CARBOCYCLIC AND L-NUCLEOSIDES workers found that 98e was active against L-1210 leukaemia cells at moderate concentrations, but pyrimidine acyclic nucleosides 99 and 100, lacking the terminal hydroxyl group were reported to be devoid of biological activity.

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Acyclic, Carbocyclic and L-Nucleosides by L. Agrofoglio, S.R. Challand

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